Tucked and Undercover
by hullosweetpea
Summary: Dean's put off telling Sam he's a drag queen (it's not like it's come up in conversations), but now Sam wants to take him to a drag show. Specifically Dean's drag show. Maybe Dean should tell him before he realizes it's his brother on stage... #Writing Prompt Wednesday. Continuation from "Sorry Not Sorry"


**A/N: On Tumblr unforth-ninawaters is doing a #WritingPromptWednesday. It's fun and you should join! This is a sequel to a past WPW piece** _ **Sorry Not**_ **Sorry, but you can pretty much read this without reading it, but I highly recommend it. Here was my prompt:**

 **My family (and/or friends) doesn't know I do drag, and it's not something I ever thought they'd accept, and now they're all excited talking about going to a show this weekend and okay, sure, it's *awesome* that they're excited about it and accepting of it but they want me to go and I'm IN that show and what will my excuse be and what if they recognize me and seriously no I cannot do this AU**

 **Disclaimer: Kripke's**

Tucked and Undercover

"Hey Dean. You wanna do something this weekend?"

Dean looked away from the movie they were watching to look at Sam. "Like what?"

Sam appeared a bit nervous and he was wringing his hands a bit. "Well, we only gone out and done a few things since I moved in with Jess…"

"Yeah."

"And it's really cool. Like the work they put in alone is astounding…"

"O _k_ ay."

"And I think you'll like it."

"Just tell me what it is Sammy."

He bit his lip and let out a deep breath. "I want to take you to a drag show."

Oh shit. "Like, drag racing, right?"

Sam groaned. " _No_ , like guys dressed as gals and gals as guys. Like RuPaul."

"RuPaul?"

"She's an amazing drag queen. But, Jess went last week and she said she saw this queen do a set to Blondie's 'One Way or Another' and apparently she does a lot of stuff with classic rock. And her name's Em Paula. You have to be a _little_ bit interested."

Dean was a whole lot of interested. His baby brother just suggested he watch _himself_ in a drag show. Small world. "I uh, can't I promised Charlie we'd have a Harry Potter movie marathon this weekend."

"C'mon Dean. Why don't you want to go?"

Because Ihave to _perform_. "Because I canceled on Charlie twice already."

"Dean, if it's a matter of being uncomfortable, don't be. Drag queens are great people."

I know. I _am_ one. And so is my boyfriend. "Sam, we can do something another time. I promise."

He settled back down on the couch looking a tad disappointed. "Okay, I just wanted to spend time with you. I miss my older brother."

Shit. Between Dean working at the garage and the shows, plus Sam's constant studying they really _hadn't_ seen much of each other. "We can hang out next weekend, promise."

"Alright. I guess I can take Jess to the drag show Saturday then."

 _Fuck._

-o-O-o-

Dean slipped the cut-off, ripped jean shorts on. "You remember me talking about Sam right?"

Cas spun in his vanity chair to face Dean. "Yeah, how is he?"

"Fine, but he wanted to hang out with me Saturday night."

Cas grabbed a bottle of white paint from the counter top of the vanity and flicked the lid open with a gloppy sound. "Did you tell him you were performing then?"

Dean sighed. "He doesn't necessarily know I've gone back into drag…or that I even did it to begin with."

Castiel squeezed paint out of the bottle and into his hands. "Why don't you?"

"I didn't know how he would take it then or now. Apparently he's completely okay with drag."

"Well, why don't you tell him after the show?"

"Maybe, I just…don't know if I'm ready."

Castiel stood up and walked over to wrap his arms around Dean's waist. "You still have time to decide. And if you need support I'll be there."

Dean smiled. "Thank you." He leaned forward and pressed his lips to Castiel's mouth. He moved closer inside Dean's space and grabbed his ass with both hands good and firm. Dean pulled away with a grin on his face. "Getting handsy now, aren't you?"

Castiel smirked at him with all teeth. "Just helping out."

Dean turned his head and looked in the full length mirror behind himself to see that Cas had left two, full spread hand prints on each cheek. He chuckled and pulled Cas back in. "What would I do without you?"

-o-O-o-

Dean finished up the last of his makeup with Castiel walked in half-dressed. "You ready for tonight?"

He spun around to see Castiel almost completely in drag. His chest was bare, but he was wearing black, high-waisted shorts, garter belts with silky black stockings slipped over his smooth legs, and lead down to sky high, midnight black stiletto heels. Castiel grinned and leaned against the doorframe, black lacey corset hanging off his finger. "I need a little help with this. If you don't mind?"

Dean set his makeup brush down and grabbed the corset from him. "I never mind sweetheart." He wrapped it around Castiel's waist and hooked the front. He wrapped the string around his hands and pulled just a tad. "You ready?"

Castiel sucked his stomach in. "Yeah." Dean pulled back and Castiel's waist was cinched in with each tug. "That's good. I still want to be able to breathe at the end of the night." Dean nodded and tied it off; Castiel letting out a deep breath. He looked at himself in the mirror. "Damn you are good."

Dean pulled his jean shorts on over his pink panties and ripped fish nets and smirked at his boyfriend. "Oh, I know I'm good."

Castiel tugged his wig cap on. "You're the fourth set tonight. And don't forget we're doing the closing act together." He picked up a roll of extreme, long lasting fashion tape, his vest top, and the most realistic boobs Dean had ever seen and he started taping _everything_. Dean never thought he would say he was watching his boyfriend affix fake breasts to his chest.

He hooked the corset around his waist and reached around for the strings to pull tight. "Okay, how's Meg doing?"

Castiel looked in the mirror, and satisfied tugged his vest top on. "Good, she's pumped to work with you tonight." He pulled the short black wig on, shaking it a bit to see if it would stick.

Jean shirt, jean jacket, and jean cuffs (there was a _lot_ of denim in this outfit). "Great, because I am so not ready. I can't believe you convinced me to actually fucking sing."

He placed a bowler hat on his head and smiled. "You sound fine. It's not every day we can ignore the actual tracks, so just roll with it and have fun."

Dean picked his Farah Fawcett wig up off the head. "I know."

Castiel looked at the time and cursed. "I have to go. I'll see you."

Dean gave him a quick peck on the cheek. "Break a leg."

Castiel pinched his ass and gave him a flirty wink before disappearing back out the door. God, what had he done right to get that man. He worked on adding the finishing touches for his outfit when he could hear the show starting.

 _Ladies and gentlemen we have a treat for you tonight. Our lovely performers will be bringing your favorite acts from the stage and screen to life. Now, without further ado, I give you Cassie Steel!_

The music swelled and the fast pace was driving.

 _You have to understand the way I am, mein herr._

Dean relaxed and focused himself while Castiel drove the crowd crazy onstage. He had watched Castiel practice earlier in the week and he still had no idea how the man was able to dance in those heels. On a fucking chair, no less. He continued to fret over his appearance as he waited for his turn to be up. All too soon Meg dropped by. "You ready, Blondie?"

Dean stood up and walked out behind Meg to backstage to where the other performers were waiting. He took a deep breath.

 _Our latest addition to our little establishment is here and you can just try and tear her down! Em Paula with our own Demon._

Dean rushed out on the stage and the first thing he noticed was that it was packed. People were cheering and clapping. It felt wonderful. The music started up and he took his cue. "Don't you know me? I'm the new Berlin wall, baby, so try and tear me down!" The crowd cheered and without wavering his smile he started to sing.

 _I was born on the other side  
Of a town ripped in two  
I made it over the great divide  
Now I'm comin' for you_

 _Enemies and adversaries  
They try and tear me down  
You want me baby, I dare you  
Try and tear me down_

He danced around the stage, flipping his hair and strutting his stuff.

 _I rose from off of the doctor's slab  
Like Lazarus from the pit  
Now everyone wants to take a stab  
And decorate me with blood graffiti and spit_

 _Enemies and adversaries  
They try and tear me down  
You want me baby, I dare you  
Try and tear me down_

He danced on stage, making the crowd scream. He mimed playing guitar and poised against other members of his "band." He leaned up against Meg as she began the exposition in the middle of the song.

 _On August 13th, 1961  
A wall was erected  
Down the middle of the city of Berlin  
The world was divided by a cold war  
And the Berlin wall  
Was the most hated symbol of that divide  
Reviled, graffitied, spit upon  
We thought the wall would stand forever_

 _And now that it's gone  
We don't know who we are anymore  
Ladies and gentlemen  
Hedwig is like that wall  
Standing before you in the divide  
Between east and west  
Slavery and freedom  
Man and woman, top and bottom_

 _And you can try and tear her down  
But before you do  
You must remember one thing_

Meg nailed her part and he took a step away from her, but held the microphone out between them to finish out the song.

 _Hey, there ain't much of a difference  
Between a bridge and a wall  
Without me right in the middle, babe  
You would be nothin' at all_

 _Enemies and adversaries  
They try and tear me down  
You want me baby, I dare you  
Try and tear me down_

 _Enemies and adversaries  
They try and tear me down  
You want me baby, I dare you  
Try and tear me down_

 _From east Berlin to junction city  
Hello New York hello Missouri  
What you try and tear me down?_

As the song came to close, Dean and Meg got more into it. He mimed playing drums and Meg strummed hard on the prop guitar they had given her, both trying to outdo each other.

 _Come on and tear, come on and tear me down_

The final chord ended and the audience was giving around an enthusiastic applause. Dean wait out too long and rushed back stage to redo his makeup and change for the finale. When he earned Castiel was already touching up the last of his makeup. He turned to face Dean and smiled. "From what I heard you nailed it out there."

Dean grinned and sat down in his chair. "Yeah, but I still got to redo all of this." He gestured to his face. He worked a makeup wipe around the parts that needed to be redone, adding a bit of extra foundation and contouring when needed, and remade his face with a bit of a more realistic female feature. He stripped out of the clothes he was wearing and slipped on a pair of white garters with sheer stockings, before stepping into the glittering, silver white dress straight out of the Roaring Twenties. He pulled out the other wig for this performance and it felt weird to be back in shorter locks after wearing the longer piece for so long. The bob was wavy and the same platinum as all his other wigs. Like Cassie Steel's beauty mark and dark hair it was part of his signature look.

Castiel smiled at him and set his long legs on the counter as he buckled his heels on. "This song isn't even that long, and I love it even more for it." He gave Dean a glance with a bit of concern. "Did you ever talk to your brother?"

Dean sighed. "No."

"Do it after this. I saw him at one of the tables with a blonde and Charlie."

"Fuck, he brought Charlie? She was my alibi for tonight."

Castiel rested a comforting hand against his face. "Just go with it. He was bound to find out sometime."

He nodded. "Okay." He let Castiel drag him back on stage for their last number. The choreography had been a bitch (Seriously, why had he agreed to it?), but it was _way_ shorter than the original and he could handle it.

 _It's the end of the night and to wrap things up welcome back Cassie Steel and Em Paula!_

The couple strutted out to the center of the stage, long coats trailing, as the music started slow and soft.

 _You can like the life you're livin'  
You can live the life you like  
You can even marry Harry  
But, mess around with Ike  
And that's good_

 _Isn't it grand? Isn't it great?  
Isn't it swell? Isn't it fun?  
Isn't it?_

 _But nothing stays in fifty years or so  
It's gonna change, you know  
But oh, it's heaven  
Nowadays_

Their movements were perfectly coordinated and as the tempo picked up they shrugged their long coats off to reveal the glimmering dresses underneath. They did a few jazz steps, all arms and legs, but the song quickly came to an end and the two grasped hands and took a bow. The audience was stomping their feet and whistling as they left the stage. Dean held tight to Castiel as they maneuvered backstage. "Do you know where they are?"

"Yeah, near the bar. Do you want me to go with you?"

He squeezed Castiel's hand tighter. "Yes, please."

They weaved their way through the crowd, hand in hand, until they found the trio. Charlie perked up and got up to hug Dean. "You rocked it up there." She let go of him and moved to tackle Castiel. "Both of you. Seriously, you guys make some _very_ sexy ladies."

Sam squinted hard at Dean and he felt his pulse race. "What can I say? I'm always sexy."

He didn't try to disguise his voice and he saw the realization dawn on Sam. " _Dean!?_ "

He shrugged his shoulders. "Surprise?" Charlie punched him in the shoulder. "OW, what was that for?"

"Making me keep this secret for so long _and_ for using me as your cover."

"Okay, maybe I deserved it."

Jess smiled. "You do make a convincing woman."

" _Thank you_ , Jess."

Castiel squeezed Dean's shoulder. "I'll leave you so you can have privacy."

Dean took his hand. "Bullshit. Guys, this is my boyfriend, Castiel."

Sam blinked. " _Oh_ , so this is the Cas you've been talking about."

Dean looked at him softly. "Yeah."

Sam crossed his arms. "How come you never told me you did drag?'

Dean sighed and rubbed his neck. "I wasn't quite sure how you would take it. I've done it for years, but I took a break. When you moved in with Jess, Charlie convinced me to get back into it and that's when I met Cas."

"I can't believe I was trying to get you to come to your own show."

"You have good taste." Sam punched his shoulder and Dean laughed. "Bitch."

"Jerk." Sam took Jess's hand and looked down at her. "Jess and I are headed out. It was nice meeting you Castiel."

He smiled. "All the same to you."

When they left Dean sighed with relief. "I should be heading out too," announced Charlie. "See ya later, bitches."

The red-head left Dean and Castiel alone as they walked backed into the dressing room. "So," started Castiel, "are there any other family members that don't know you do drag?"

"They don't get to know. It's not like it would come up in a normal conversation."

"I just wanted to make sure." Castiel leaned in and pressed a kiss to his lips. "Anytime you want me to be there, just let me know."

Dean rolled his eyes, with a smile on his face. "Just shut up and get changed so we can go back to my place. I have plans for you."

Castiel smiled wickedly at him and pulled him in closer. "I can work with that."

They kissed, makeup smearing and wigs skewed.

 **A/N: Songs used. "Mein Herr" –** _ **Cabaret,**_ **"Tear Me Down" –** _ **Hedwig and the Angry Inch,**_ **"Nowadays" –** _ **Chicago.**_ **Hope you all enjoyed.**


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